Herbicidal substituted 4-sulphonylamino-2-azinyl-2,4-triazol-3-ones

ABSTRACT

Herbicidal substituted sulphonylaminotriazolinones of the formula ##STR1## in which R 1  represents an optionally substituted radical from the group consisting of alkyl, aralkyl, aryl and heteroaryl, 
     R 2  represents hydrogen or the group --SO 2  --R 1  where R 1  has the abovementioned meaning, 
     R 3  represents hydrogen, halogen, hydroxyl, mercapto, amino or an optionally substituted radical from the group consisting of alkyl, cycloalkyl, aralkyl, aryl alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, aralkoxy, aralkylthio, alkylamino and dialkylamino, 
     R 4  represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino, 
     X represents nitrogen or a CH group, 
     Y represents nitrogen or a CR 5  group where 
     R 5  represents hydrogen, halogen, cyano, alkyl, formyl, alkylcarbonyl or alkoxycarbonyl, and 
     Z represents nitrogen or a CR 6  group where 
     R 6  represents hydrogen, halogen, hydroxyl, amino or an optionally substituted radical from the group consisting of alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino, 
     and salts thereof. Intermediates of the formulas ##STR2## are also new.

This is a division of application Ser. No. 382,163, filed July 19, 1989,now issued U.S. Pat. No. 4,988,381. .spsb.

The invention relates to new substituted4-sulphonylamino-2-azinyl-1,2,4-triazol-3-ones (hereinafter abbreviatedto "substituted sulphonylaminotriazolinones"), processes and newintermediates for their preparation, and their use as herbicides.

It has been disclosed that certain substituted triazolinones, such as,for example,4-(3-trifluoromethoxybenzylideneamino)-2,4-dihydro-3H-1,2,4-triazol-3-one,are herbicidally active (cf. U.S. Pat. No. 3,884,910). However, theaction of these known compounds is not satisfactory in all respects.

The new substituted sulphonylaminotriazolinones of the general formula(I) ##STR3## in which R¹ represents an optionally substituted radicalfrom the series comprising alkyl, aralkyl, aryl and heteroaryl,

R² represents hydrogen or the group --SO₂ --R¹ where R¹ has theabovementioned meaning,

R³ represents hydrogen, halogen, hydroxyl, mercapto, amino or anoptionally substituted radical from the series comprising alkyl,cycloalkyl, aralkyl, aryl, alkoxy, alkenyloxy, alkinyloxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkenylthio, alkinylthio, aralkoxy,aralkylthio, alkylamino and dialkylamino,

R⁴ represents hydrogen, halogen, hydroxyl, amino or an optionallysubstituted radical from the series comprising alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino,

X represents nitrogen or a CH group,

Y represents nitrogen or a CR⁵ group where

R⁵ represents hydrogen, halogen, cyano, alkyl, formyl, alkylcarbonyl oralkoxycarbonyl, and

Z represents nitrogen or a CR⁶ group where

R⁶ represents hydrogen, halogen, hydroxyl, amino or an optionallysubstituted radical from the series comprising alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino and dialkylamino,

and salts of compounds of the formula (I) have now been

The new substituted sulphonylaminotriazolinones of the general formula(I) are obtained when

(a) substituted aminotriazolinones of the general formula (II) ##STR4##in which R³, R⁴, X, Y and Z have the abovementioned meanings,

are reacted with sulphonyl halides or sulphonic anhydrides of thegeneral formula (III)

    R.sup.1 --SO.sub.2 --Q                                     (III)

in which

R¹ has the abovementioned meaning and

Q represents fluorine, chlorine, bromine or the group --O--SO₂ --R¹,where

R¹ has the abovementioned meaning,

if appropriate, in the presence of an acid acceptor and, if appropriate,in the presence of a diluent, the resulting compounds of the formula (I)in which

R² represents the group --SO₂ --R¹,

are reacted, if appropriate, with desulphonylating agents, ifappropriate in the presence of diluents, to give compounds of theformula (I) in which

R² represents hydrogen,

and, if appropriate, salts are prepared therefrom by customary methodsor when

b) sulphonylaminotriazolinones of the general formula (IV) ##STR5## inwhich R¹, R² and R³ have the above-mentioned meanings, are reacted withazines of the general formula (V) ##STR6## in which R⁴, X, Y and Z havethe above-mentioned meanings and

Q¹ represents halogen, benzylsulphonyl or alkylsulphonyl, ifappropriate, in the presence of an acid acceptor and, if appropriate, inthe presence of a diluent and, if appropriate, salts are prepared bycustomary methods from the resultant compounds of the formula (I).

The new substituted sulphonylaminotriazolinones of the general formula(I) are distinguished by powerful herbicidal activity. These compoundsrepresent a chemically novel class of herbicides. Surprisingly, the newcompounds of the formula (I) show a considerably better herbicidalaction than4-(3-trifluoromethoxy-benzylideneamino)-2,4-dihydro-3H-1,2,4-triazol-3-one,which is known and has similar structure.

The invention preferably relates to compounds of the formula (I) inwhich

R¹ represents the radical ##STR7## where R⁷ and R⁸ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, iodine,cyano, nitro, C₁ -C₆ -alkyl [which is optionally substituted byfluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁-C₄ -alkylaminocarbonyl, di-(C₁ -C₄ -alkyl)aminocarbonyl, hydroxyl, C₁-C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄-alkoxycarbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄-alkyl)aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl], represent C₂ -C₆-alkenyl [which is optionally substituted by fluorine, chlorine,bromine, cyano, C₁ -C₄ -alkoxycarbonyl, carboxyl or phenyl], representC₂ -C₂ -C₆ -alkinyl [which is optionally substituted by fluorine,chlorine, bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl],represent C₁ -C₄ -alkoxy [which is optionally substituted by fluorine,chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄-alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl], represent C₁ -C₄ -alkylthio [which is optionallysubstituted by fluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄-alkoxy-carbonyl, C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl], represent C₃ -C₆ -alkenyloxy [which is optionallysubstituted by fluorine, chlorine, bromine, cyano or C₁ -C₄ -cyano or C₁-C-₄ -alkoxy-carbonyl], represent C₂ -C₆ -alkenylthio [which isoptionally substituted by fluorine, chlorine, bromine, cyano, nitro, C₁-C₃ -alkylthio or C₁ -C₄ -alkoxycarbonyl], C₃ -C₆ -alkinyloxy, C₃ -C₆-alkinylthio or represent the radical --S(0)_(p) --R⁹, where

p represents the numbers 1 or 2 and

R⁹ represents fluorine, C₁ -C₄ -alkyl [which is optionally substitutedby fluorine, chlorine, bromine, cyano or C₁ -C₄ -alkoxy-carbonyl], C₃-C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkoxy-C₁ -C₄-alkylamino, C₁ -C₄ -alkylamino, di(C₁ -C₄ -alkyl)-amino or representsthe radical --NHOR¹⁰, where

R¹⁰ represents C₁ -C₆ -alkyl [which is optionally substituted byfluorine, chlorine, cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylaminocarbonyl or di-(C₁ -C₄-alkyl)amino-carbonyl], represents C₃ -C₆ -alkenyl [which is optionallysubstituted by fluorine, chlorine or bromine], C₃ -C₆ -alkinyl, C₃ -C₆-cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂ -alkyl, phenyl-C₁ -C₂ -alkyl[which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁-C₄ -alkyl, C₁ -C₄ -alkoxy or C₁ -C₄ -alkoxy-carbonyl], representsbenzhydryl or represents phenyl [which is optionally substituted byfluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, trifluoromethyl, C₁ -C₄-alkoxy, C₁ -C₂ -fluoroalkoxy, C₁ -C₄ -alkylthio, trifluoromethylthio orC₁ -C₄ -alkoxycarbonyl],

R⁷ and/or R⁸ furthermore represent phenyl or phenoxy, C₁ -C₄-alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄-alkylaminocarbonyl-amino, di-(C₁ -C₄ -alkyl)-aminocarbonylamino, orrepresent the radical --CO--R¹¹, where

R¹¹ represents C₁ -C₆ -alkyl, C₁ -C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃-C₆ -alkenyloxy, C₁ -C₄ - alkylthio, C₁ -C₄ -alkylamino, C₁ -C₄-alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄ -alkyl-amino or di-(C₁ -C₄-alkyl)-amino [which are optionally substituted by fluorine and/orchlorine],

R⁷ and/or R⁸ furthermore represent C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄-alkyl)-aminosulphonylamino or the radical --CH═N--R¹², where

R¹² represents C₁ -C₆ -alkyl which is optionally substituted byfluorine, chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, represents benzylwhich is optionally substituted by fluorine or chlorine, represents C₃-C₆ -alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substitutedby fluorine or chlorine, represents phenyl which is optionallysubstituted by fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄-alkoxy, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,represents C₁ -C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy orbenzyloxy, each of which is optionally substituted by fluorine and/orchlorine, represents amino, C₁ -C₄ -alkylamino, di-(C₁ -C₄-alkyl)-amino, phenylamino, C₁ -C₄ -alkyl-carbonylamino, C₁ -C₄-alkoxy-carbonylamino, C₁ -C₄ -alkylsulphonylamino or representsphenylsulphonylamino which is optionally substituted by fluorine,chlorine, bromine or methyl,

where furthermore

R¹ represents the radical ##STR8## where R¹³ represents hydrogen or C₁-C₄ -alkyl,

R¹⁴ and R¹⁵ are identical or different and represent hydrogen, fluorine,chlorine, bromine, nitro, cyano, C₁ -C₄ -alkyl [which is optionallysubstituted by fluorine and/or chlorine], C₁ -C₄ -alkoxy [which isoptionally substituted by fluorine and/or chlorine], carboxyl, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkylsulphonyl or di-(C₁ -C₄-alkyl)-aminosulphonyl; where furthermore

R¹ represents the radical ##STR9## where R¹⁶ and R¹⁷ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl [which is optionally substituted by fluorine and/orchlorine] or C₁ -C₄ -alkoxy [which is optionally substituted by fluorineand/or chlorine]; where furthermore

R¹ represents the radical ##STR10## where R¹⁸ and R¹⁹ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, nitro,cyano, C₁ -C₄ -alkyl [which is optionally substituted by fluorine and/orchlorine], C₂ -C₄ -alkenyl [which is optionally substituted by fluorineand/or chlorine], C₁ -C₄ -alkoxy [which is optionally substituted byfluorine and/or chlorine], represents C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl or C₁ -C₄ -alkylsulphonyl [which are optionallysubstituted by fluorine and/or chlorine], and represents di-(C₁ -C₄-alkyl)-aminosulphonyl, C₁ -C₄ -alkoxy-carbonyl, dimethylaminocarbonylor dioxolanyl; where furthermore

R¹ represents the radical ##STR11## where R²⁰ and R²¹ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, C₁ -C₄-alkyl [which is optionally substituted by fluorine and/or bromine], C₁-C₄ -alkoxy [which is optionally substituted by fluorine and/orchlorine], represent C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄-alkylsulphonyl [which are optionally substituted by fluorine and/orchlorine], or represent di-(C₁ -C₄ -al-kyl)-aminosulphonyl; wherefurthermore

R¹ represents the radical ##STR12## where R²² and R²³ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, cyano,nitro, C₁ -C₄ -alkyl [which is optionally substituted by fluorine,chlorine, C₁ -C₄ -alkoxy and/or C₁ -C₄ -halogenoalkoxy], C₁ -C₄ -alkoxy[which is optionally substituted by fluorine and/or chlorine], C₁ -C₄-alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl [which isoptionally substituted by fluorine and/or chlorine], di-(C₁ -C₄-alkyl)-aminosulphonyl or C₁ -C₄ -alkoxycarbonyl, and

A represents oxygen, sulphur or the group N--Z¹, where

Z¹ represents hydrogen, C₁ -C₄ -alkyl [which is optionally substitutedby fluorine, chlorine, bromine or cyano], C₃ -C₆ -cycloalkyl, benzyl,phenyl [which is optionally substituted by fluorine, chlorine, bromineor nitro], C₁ -C₄ -alkylcarbonyl, C₁ -C₄ -alkoxy-carbonyl or di-(C₁ -C₄-alkyl)-aminocarbonyl; where furthermore

R¹ represents the radical ##STR13## where R²⁴ and R²⁵ are identical ordifferent and represent hydrogen, C₁ -C₄ -alkyl, halogen, C₁ -C₄-alkoxycarbonyl, C₁ -C₄ -alkoxy or C₁ -C₄ -halogenoalkoxy,

Y¹ represents sulphur or the group N--R²⁶, where

R²⁶ represents hydrogen or C₁ -C₄ -alkyl; where furthermore

R¹ represents the radical ##STR14## where R²⁷ represents hydrogen, C₁-C₄ -alkyl, benzyl, (iso)quinolinyl or phenyl,

R²⁸ represents hydrogen, halogen, cyano, nitro, C₁ -C₄ -alkyl [which isoptionally substituted by fluorine and/or chlorine], C₁ -C₄ -alkoxy[which is optionally substituted by fluorine and/or chlorine],dioxolanyl or C₁ -C₄ -alkoxy-carbonyl and

R²⁹ represents hydrogen, halogen or C₁ -C₄ -alkyl; where furthermore

R¹ represents the radical ##STR15## where R³⁰ represents hydrogen,halogen, C₁ -C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-halogenoalkoxy or C₁ -C₄ -alkoxy-carbonyl; where furthermore

R¹ represents the radical ##STR16## where R³¹ represents C₁ -C₄ -alkyland

R³² represents C₁ -C₄ -alkyl; where furthermore

R¹ represents the radical ##STR17## where R³³ represents hydrogen ormethyl

in which furthermore

R² represents hydrogen or the group --SO₂ --R¹, where

R¹ has the meaning indicated above as preferred; in which furthermore

R³ represents hydrogen, fluorine, chlorine, bromine, iodine, hydroxyl,mercapto, amino or an optionally fluorine- and/or chlorine-substitutedradical from the series comprising C₁ -C₄ -alkyl, C₃ -C₆ -cycloalkyl,benzyl, phenyl, C₁ -C₄ -alkoxy, C₃ -C₄ -alkenyloxy, C₃ -C₄ -alkinyloxy,C₁ -C₄ -alkylthio, 11-C4-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₃ -C₄-alkenylthio, C₃ -C₄ -alkinylthio, benzyloxy, benzylthio, C₁ -C₄-alkylamino and di-(C₁ -C₄ -alkyl)-amino,

R⁴ represents hydrogen, fluorine, chlorine, bromine, hydroxyl, amino, C₁-C₄ -alkyl, C₁ -C₄ -halogenoalkyl, C₁ -C₂ -alkoxy-C₁ -C₂ -alkyl, C₁ -C₄-alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₂ -alkoxy-C₁ -C₂ -alkoxy, C₁ -C₄-alkylthio, C₁ -C₄ -halogenoalkylthio, C₁ -C₄ -alkylsulphinyl, C₁ -C₄-alkylsulphonyl, C₁ -C₄ alkylamino or di-(C₁ -C₂ -alkyl)-amino,

X represents nitrogen or a CH group,

Y represents nitrogen or a CR⁵ group where

R⁵ represents hydrogen, fluorine, chlorine, bromine, cyano, methyl,formyl, acetyl, methoxycarbonyl or ethoxycarbonyl and

Z represents nitrogen or a CR⁶ group where

R⁶ represents hydrogen, fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁-C₄ -alkoxy, C₁ -C₄ -halogenoalkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₁ -C₄ -alkylamino,dimethylamino or diethylamino.

The invention particularly relates to compounds of the formula (I) inwhich

R¹ represents the radical ##STR18## where R⁷ represents fluorine,chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy,trifluoromethoxy, C₁ -C₃ -alkylthio, C₁ -C₃ -alkylsulphinyl, C₁ -C₃-alkylsulphonyl, dimethylaminosulphonyl,N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy or C₁ -C₃-alkoxycarbonyl and

R⁸ represents hydrogen, fluorine or chlorine; where furthermore

R¹ represents the radical ##STR19## where R¹³ represents hydrogen,

R¹⁴ represents fluorine, chlorine, bromine, methyl, methoxy,difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and

R¹⁵ represents hydrogen; where furthermore

R¹ represents the radical ##STR20## where R represents C₁ -C₄ -alkyl, or

R¹ represents the radical ##STR21## where R represents C₁ -C₄ -alkyl, or

R¹ represents the radical ##STR22## where R³⁰ represents hydrogen,chlorine, methyl, ethyl, methoxycarbonyl or ethoxycarbonyl;

in which furthermore

R² represents hydrogen or for the group --SO₂ --R¹, wherein

R¹ has the meaning indicated above as being particularly preferred,

R³ represents hydrogen, methyl, ethyl, propyl, isopropyl,trifluoromethyl, cyclopropyl, benzyl, phenyl, t-butyl, s-butyl, i-butly,n-butyl, methoxy or methylthio,

R⁴ represents hydrogen, fluorine, chlorine, bromine, methyl,trifluoromethyl, methoxy, ethoxy, difluoromethoxy, methylthio,ethylthio, amino, methylamino, ethylamino, dimethylamino ordiethylamino,

X represents nitrogen or a CH group,

Y represents nitrogen or a CR⁵ group where

R² represents hydrogen, fluorine, chlorine or methyl, and

Z represents nitrogen or a CR⁶ group where

R⁶ represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl,methoxy, ethoxy, propoxy, isopropoxy, difluoromethoxy, methylthio,ethylthio, methylamino, ethylamino, dimethylamino or diethylamino.

The invention furthermore preferably relates to salts of compounds ofthe formula (I)

α) with proton acids, such as, for example, hydrochloric acid, sulphuricacid, phosphoric acid, methanesulphonic acid, benzene- orp-toluenesulphonic acid, or naphthalene-mono- or -di-sulphonic acids, or

β) with bases, such as, for example, sodium hydroxide, potassiumhydroxide, calcium hydroxide, sodium hydride, potassium hydride, calciumhydride, sodium amide, potassium amide, calcium amide, sodium carbonate,potassium carbonate or calcium carbonate, sodium C₁ -C₄ -alkanoxides orpotassium C₁ -C₄ -alkanoxides, ammonia, C₁ -C₄ -alkylamines, di-(C₁ -C₄-alkyl)amines or tri-(C₁ -C₄ -alkyl)-amines.

If, for example,4-amino-5-methyl-2-(4,6-dimethoxy-s-triazin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneand 2-fluoro-benzenesulphonyl chloride (at least two mole equivalents)are used as starting substances in process (a) according to theinvention, the course of the reaction in process (a) according to theinvention can be outlined by the following equation: ##STR23##

If, for example,4-(2-difluormethoxy-phenylsulphonylamino)-5-trifluormethyl-2,4-dihydro-3H-1,2,4-triazol-3-oneand 4,6-dimethoxy-2-methylsulphonyl-pyrimidine are used as startingsubstances in process (b) according to the invention, the course of thereaction in process (b) according to the invention can be outlined bythe following equation: ##STR24##

Formula (II) provides a general definition of the substitutedaminotriazolinones to be used as starting substances in the process (a)according to the invention for the preparation of compounds of theformula (I).

In formula (II), R³, R⁴, X, Y and Z preferably, or in particular, havethose meanings which have already been mentioned above in connectionwith the description of the compounds of the formula (I) according tothe invention as being preferred, or particularly preferred, for R³, R⁴,X, Y and Z.

Examples of the starting substances of the formula (II) are listed inTable 1 below.

                  TABLE 1                                                         ______________________________________                                        Examples of the starting substances of the formula (II)                       R.sup.3   R.sup.4    X       Y     Z                                          ______________________________________                                        H         CH.sub.3   N       CH    CCH.sub.3                                  H         CH.sub.3   N       CH    COCH.sub.3                                 H         CH.sub.3   N       CH    COC.sub.2 H.sub.5                          H         OCH.sub.3  N       CH    COCH.sub.3                                 H         OCH.sub.3  N       CH    CCl                                        H         H          N       CH    CCH.sub.3                                  H         CF.sub.3   N       CH    CCH.sub.3                                  H         CF.sub.3   N       CH    COCH.sub.3                                 H         CF.sub.3   N       CH    CCF.sub.3                                  H         OCH.sub.3  N       CH    COCHF.sub.2                                H         CH.sub.3   N       CH    COCHF.sub.2                                H         OCHF.sub.2 N       CH    COCHF.sub.2                                H         CH.sub.3   N       N     COCH.sub.3                                 H         OCH.sub.3  N       N     COCH.sub.3                                 H         OCH.sub.3  N       N     CCl                                        H         C.sub.2 H.sub.5                                                                          N       CH    COCH.sub.3                                 H         C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 CH.sub.3  CH.sub.3   N       CH    CCH.sub.3                                  CH.sub.3  CH.sub.3   N       CH    COCH.sub.3                                 CH.sub.3  OCH.sub.3  N       CH    COCH.sub.3                                 CH.sub.3  OCH.sub. 3 N       CH    CCl                                        CH.sub.3  OCHF.sub.2 N       CH    COCHF.sub.2                                CH.sub.3  H          N       CH    CCH.sub.3                                  CH.sub.3  CF.sub.3   N       CH    CCH.sub.3                                  CH.sub.3  CF.sub.3   N       CH    COCH.sub.3                                 CH.sub.3  CF.sub.3   N       CH    CCF.sub.3                                  CH.sub.3  OCH.sub.3  N       CH    COCHF.sub.2                                CH.sub.3  Cl         N       CH    COCHF.sub.2                                CH.sub.3  CH.sub.3   N       CH    COCHF.sub.2                                CH.sub.3  NHCH.sub.3 N       CH    COCH.sub.3                                 CH.sub.3  CH.sub.3   N       N     CCH.sub.3                                  CH.sub.3  CH.sub.3   N       N     COCH.sub.3                                 CH.sub.3  OCH.sub.3  N       N     COCH.sub.3                                 CH.sub.3  C.sub.2 H.sub.5                                                                          N       CH    COCH.sub.3                                 CH.sub.3  CH.sub.3   N       N     COC.sub.2 H.sub.5                          CH.sub.3  C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 CH.sub.3  CH.sub.3   N       N     CCl                                        CH.sub.3  CH.sub.3   CH      N     CCH.sub.3                                  CH.sub.3  OCH.sub.3  CH      N     COCH.sub.3                                 CH.sub.3  CH.sub.3   N       CH    CSCH.sub.3                                 H         CH.sub.3   N       CH    CN(CH.sub.3).sub.2                         H         OCH.sub.3  N       CH    CSCH.sub.3                                 H         OCH.sub. 3 N       N     CNHC.sub.2 H.sub.5                         H         OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                H         CH.sub.3   CH      CH    CCH.sub.3                                  OCH.sub.3 CH.sub.3   N       CH    CCH.sub.3                                  OCH.sub.3 CH.sub.3   N       CH    COCH.sub.3                                 OCH.sub.3 OCH.sub.3  N       CH    COCH.sub.3                                 OCH.sub.3 OCH.sub.3  N       CH    CCl                                        OCH.sub.3 H          N       CH    CCH.sub.3                                  OCH.sub.3 CF.sub.3   N       CH    COCH.sub.3                                 OCHF.sub.2                                                                              OCH.sub.3  N       CH    COCHF.sub.2                                OCH.sub.3 CH.sub.3   N       CH    COCHF.sub.2                                OCH.sub.3 CH.sub.3   N       N     CCH.sub.3                                  OCH.sub.3 CH.sub.3   N       N     COCH.sub.3                                 OCH.sub.3 OCH.sub.3  N       N     COCH.sub.3                                 OCH.sub.3 C.sub.2 H.sub.5                                                                          N       CH    COCH.sub.3                                 OCH.sub.3 C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 SCH.sub.3 CH.sub.3   N       CH    CCH.sub.3                                  OCH.sub.3 CH.sub.3   N       N     COC.sub.2 H.sub.5                          SCH.sub.3 CH.sub.3   N       CH    COCH.sub.3                                 SCH.sub.3 CH.sub.3   N       CH    COC.sub.2 H.sub.5                          SCH.sub.3 OCH.sub.3  N       CH    COCH.sub.3                                 SCH.sub.3 OCH.sub.3  N       CH    CCl                                        SCH.sub.3 H          N       CH    CCH.sub.3                                  SCH.sub.3 CF.sub.3   N       CH    CCF.sub.3                                  SCH.sub.3 CF.sub.3   N       CH    COCH.sub.3                                 SCH.sub.3 CF.sub.3   N       CH    CCH.sub.3                                  SCH.sub.3 OCH.sub.3  N       CH    COCHF.sub.2                                SCH.sub.3 CH.sub.3   N       CH    COCHF.sub.2                                SCH.sub.3 OCHF.sub.2 N       CH    COCHF.sub.2                                SCH.sub.3 NHCH.sub.3 N       CH    COCH.sub.3                                 SCH.sub.3 CH.sub.3   N       N     CCH.sub.3                                  SCH.sub.3 CH.sub.3   N       N     COCH.sub.3                                 SCH.sub.3 OCH.sub.3  N       N     COCH.sub.3                                 SCH.sub.3 OCH.sub.3  N       N     CCl                                        SCH.sub.3 C.sub.2 H.sub.5                                                                          N       CH    COCH.sub.3                                 SCH.sub.3 C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 SCH.sub.3 OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         SCH.sub.3 OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.2 H.sub.5                                                                         CH.sub.3   N       CH    CCH.sub.3                                  C.sub.2 H.sub.5                                                                         CH.sub.3   N       CH    COCH.sub.3                                 C.sub.2 H.sub.5                                                                         CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.2 H.sub.5                                                                         OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.2 H.sub.5                                                                         OCH.sub.3  N       CH    CCl                                        C.sub.2 H.sub.5                                                                         H          N       CH    CCH.sub.3                                  C.sub.2 H.sub.5                                                                         CF.sub.3   N       CH    CCH.sub.3                                  C.sub.2 H.sub.5                                                                         CF.sub.3   N       CH    COCH.sub.3                                 C.sub.2 H.sub.5                                                                         CF.sub.3   N       CH    CCF.sub.3                                  C.sub.2 H.sub.5                                                                         OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.2 H.sub.5                                                                         CH.sub.3   N       CH    COCHF.sub.2                                C.sub.2 H.sub.5                                                                         OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.2 H.sub.5                                                                         NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.2 H.sub.5                                                                         CH.sub.3   N       N     CCH.sub.3                                  C.sub.2 H.sub.5                                                                         CH.sub.3   N       N     COCH.sub.3                                 C.sub.2 H.sub.5                                                                         OCH.sub.3  N       N     COCH.sub.3                                 C.sub.2 H.sub.5                                                                         C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.2 H.sub.5                                                                         CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.2 H.sub.5                                                                         OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.2 H.sub.5                                                                         OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -n                                                                      CH.sub. 3  N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.3 H.sub.7 -n                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.3 H.sub.7 -n                                                                      H          N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -n                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -n                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.3 H.sub.7 -n                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -n                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -n                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -n                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub. 2                        C.sub.3 H.sub.7 -n                                                                      OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.3 H.sub.7 -n                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.3 H.sub.7 -i                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.3 H.sub.7 -i                                                                      H          N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -i                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.3 H.sub.7 -i                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.3 H.sub.7 -i                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -i                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.3 H.sub.7 -i                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.3 H.sub. 7 -i                                                                     CH.sub.3   N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.3 H.sub.7 -i                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.3 H.sub.7 -i                                                                      OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.3 H.sub.7 -i                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                 ##STR25##                                                                              CH.sub.3   N       CH    CCH.sub.3                                   ##STR26##                                                                              CH.sub.3   N       CH    COCH.sub.3                                  ##STR27##                                                                              CH.sub.3   N       CH    COC.sub.2 H.sub.5                           ##STR28##                                                                              OCH.sub.3  N       CH    COCH.sub.3                                  ##STR29##                                                                              OCH.sub.3  N       CH    CCl                                         ##STR30##                                                                              H          N       CH    CCH.sub.3                                   ##STR31##                                                                              CF.sub.3   N       CH    CCH.sub.3                                   ##STR32##                                                                              CF.sub.3   N       CH    COCH.sub.3                                  ##STR33##                                                                              CF.sub.3   N       CH    CCF.sub.3                                   ##STR34##                                                                              OCH.sub.3  N       CH    COCHF.sub.2                                 ##STR35##                                                                              CH.sub.3   N       CH    COCHF.sub.2                                 ##STR36##                                                                              OCHF.sub.2 N       CH    COCHF.sub.2                                 ##STR37##                                                                              NHCH.sub.3 N       CH    COCH.sub.3                                  ##STR38##                                                                              CH.sub.3   N       N     CCH.sub.3                                   ##STR39##                                                                              CH.sub.3   N       N     COCH.sub.3                                  ##STR40##                                                                              OCH.sub.3  N       N     COCH.sub.3                                  ##STR41##                                                                              C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                  ##STR42##                                                                              CH.sub.3   N       N     CN(CH.sub.3).sub.2                          ##STR43##                                                                              OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                          ##STR44##                                                                              OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.4 H.sub.9 -n                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.4 H.sub.9 -n                                                                      H          N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -n                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -n                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.4 H.sub.9 -n                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -n                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -n                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -n                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.4 H.sub.9 -n                                                                      OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.4 H.sub.9 -n                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.4 H.sub.9 -s                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.4 H.sub.9 -s                                                                      H          N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -s                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -s                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.4 H.sub.9 -s                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -s                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -s                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -s                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.4 H.sub.9 -s                                                                      OCH.sub. 3 N       N     CNHC.sub.2 H.sub.5                         C.sub.4 H.sub.9 -s                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       CH.sub.3                                                                            CCH.sub.3                                  C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.4 H.sub.9 -i                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.4 H.sub.9 -i                                                                      H          N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -i                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -i                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.4 H.sub.9 -i                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -i                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -i                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -i                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.4 H.sub.9 -i                                                                      OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.4 H.sub.9 -i                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       CH    COC.sub.2 H.sub.5                          C.sub.4 H.sub.9 -t                                                                      OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      OCH.sub.3  N       CH    CCl                                        C.sub.4 H.sub.9 -t                                                                      H          N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -t                                                                      CF.sub.3   N       CH    CCH.sub.3                                  C.sub.4 H.sub.9 -t                                                                      CF.sub.3   N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      CF.sub.3   N       CH    CCF.sub.3                                  C.sub.4 H.sub.9 -t                                                                      OCH.sub.3  N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -t                                                                      OCHF.sub.2 N       CH    COCHF.sub.2                                C.sub.4 H.sub.9 -t                                                                      NHCH.sub.3 N       CH    COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       N     CCH.sub.3                                  C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      OCH.sub.3  N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 C.sub.4 H.sub.9 -t                                                                      CH.sub.3   N       N     CN(CH.sub.3).sub.2                         C.sub.4 H.sub.9 -t                                                                      OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         C.sub.4 H.sub.9 -t                                                                      OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                CF.sub.3  CH.sub.3   N       CH    CCH.sub.3                                  CF.sub.3  CH.sub.3   N       CH    COCH.sub.3                                 CF.sub.3  CH.sub.3   N       CH    COC.sub.2 H.sub.5                          CF.sub.3  OCH.sub.3  N       CH    COCH.sub.3                                 CF.sub.3  OCH.sub.3  N       CH    CCl                                        CF.sub.3  H          N       CH    CCH.sub.3                                  CF.sub.3  CF.sub.3   N       CH    CCH.sub.3                                  CF.sub.3  CF.sub.3   N       CH    COCH.sub.3                                 CF.sub.3  CF.sub.3   N       CH    CCF.sub.3                                  CF.sub.3  OCH.sub.3  N       CH    COCHF.sub.2                                CF.sub.3  CH.sub.3   N       CH    COCHF.sub.2                                CF.sub.3  OCHF.sub.2 N       CH    COCHF.sub.2                                CF.sub.3  NHCH.sub.3 N       CH    COCH.sub.3                                 CF.sub.3  CH.sub.3   N       N     CCH.sub.3                                  CF.sub.3  CH.sub.3   N       N     COCH.sub.3                                 CF.sub.3  OCH.sub.3  N       N     COCH.sub.3                                 CF.sub.3  C.sub.2 H.sub.5                                                                          N       N     COCH.sub.3                                 CF.sub.3  CH.sub.3   N       N     CN(CH.sub.3).sub.2                         CF.sub.3  OCH.sub.3  N       N     CNHC.sub.2 H.sub.5                         CF.sub.3  OC.sub.2 H.sub.5                                                                         N       N     CNHCH.sub.3                                C.sub.6 H.sub.5                                                                         CH.sub.3   N       CH    CCH.sub.3                                  C.sub.6 H.sub.5                                                                         CH.sub.3   N       CH    COCH.sub.3                                 C.sub.6 H.sub.5                                                                         OCH.sub.3  N       CH    COCH.sub.3                                 C.sub.6 H.sub.5                                                                         OCH.sub.3  N       CH    CCl                                        C.sub.6 H.sub.5                                                                         CH.sub.3   N       N     COCH.sub.3                                 C.sub.6 H.sub.5                                                                         OCH.sub.3  N       N     COCH.sub.3                                 CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3   N       CH    CCH.sub.3                                  CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3   N       CH    COCH.sub.3                                 CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3  N       CH    COCH.sub.3                                 CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3  N       CH    CCl                                        CH.sub.2 C.sub.6 H.sub.5                                                                CH.sub.3   N       N     COCH.sub.3                                 CH.sub.2 C.sub.6 H.sub.5                                                                OCH.sub.3  N       N     COCH.sub.3                                 ______________________________________                                    

The substituted aminotriazolinones of the formula (II), which are to beused as starting substances in process (a), were hitherto unknown fromthe literature. The new compounds of the formula (II) are obtained when

(α) aminotriazolinones of the general formula (VI) ##STR45## in which R³has the abovementioned meaning,

are reacted at temperatures between 20° C. and 150° C., if appropriate,with carbonyl compounds of the general formula (VII) ##STR46## in whichA¹ represents hydrogen or alkyl and

A² represents alkyl or aryl,

if appropriate in the presence of a catalyst, such as, for example,sulphuric acid, methanesulphonic acid or p-toluenesulphonic acid, and ifappropriate in the presence of a diluent, such as, for example,methylene chloride, toluene, xylene, methanol, ethanol or isopropanol,

the alkylideneaminotriazolinones (some of which are new) formed in thisprocess of the general formula (VIII) ##STR47## in which A¹, A² and R³have the abovementioned meanings, are, if appropriate, isolated and/orreacted virtually in situ, that is to say after concentrating thereaction mixture, with azines of the general formula (V) ##STR48## inwhich R⁴, X, Y and Z have the abovementioned meanings and

Q¹ represents halogen, benzylsulphonyl or alkylsulphonyl,

if appropriate in the presence of an acid acceptor, such as, forexample, potassium carbonate, and if appropriate in the presence of adiluent, such as, for example, acetonitrile or dimethylformamide, attemperatures between 0° C. and 150° C.

and the (new) substituted alkylideneaminotriazolinones formed in thisprocess, of the general formula (IX) ##STR49## in which A¹, A², A³, R⁴,X, Y and Z have the abovementioned meanings,

are hydrolyzed in a customary manner, for example by reacting them withwater, if appropriate in the presence of an organic solvent, such as,for example, methanol, ethanol, isopropanol or dioxane, and ifappropriate in the presence of an acid, such as, for example,hydrochloric acid or sulphuric acid, at temperatures between 20° C. and100° C. to give the compounds of the formula (II); or when

(β) oxadiazolones of the general formula (X) ##STR50## in which R³ hasthe abovementioned meaning,

are reacted with azines of the general formula (V) -above

if appropriate in the presence of an acid acceptor, such as, forexample, potassium carbonate, and if appropriate in the presence of adiluent, such as, for example, acetonitrile, dioxane ordimethylformamide, at temperatures between 0° C. and 150° C.

and the (new) substituted oxadiazolones formed in this process, of thegeneral formula (XI) ##STR51## in which R³, R⁴, X, Y and Z have theabovementioned meanings,

are reacted with hydrazine or hydrazine hydrate at temperatures between0° C. and 150° C.

Some of the compounds of the formula (II) can be prepared using asynthesis route similar to the one described under (α) but withoutintroducing protective groups using carbonyl compounds of the formula(VII), that is to say by directly reacting compounds of the formula (VI)with compounds of the formula (V) under the reaction conditionsindicated under (α).

Formula (VI) provides a general definition of the aminotriazolinones,which are required as intermediates. In formula (VI), R³ preferably, orin particular, has the meaning which has already been indicated above inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, or particularlypreferred, for R³.

Example of the compounds of the formula (VI) which may be mentioned are:

4-amino-2,4-dihydro-3-H-1,2,4-triazol-3-one,4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-ethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-cyclopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-isopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one,4-amino-5-isobutyl-2,4-dihydro-3H-1,2,4-triazol-3-one and4-amino-5-tert.-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

The aminotriazolinones of the formula (VI) are known and/or can beprepared by processes known per se (cf. Chem. Ber. 98 (1965), 3025-3033;J.Heterocycl. Chem. 21 (1984), 1769-1774; Doga: Kim. Ser. 10 (1986),34-39 -quoted in Chem. Abstracts 106: (1987), 138338e).

Formula (VII) provides a definition of the carbonyl compounds alsorequired as intermediates.

In formula (VII),

A¹ preferably represents hydrogen or methyl and

A² preferably represents methyl, ethyl, propyl, isopropyl, butyl,isobutyl or phenyl.

Examples of the compounds of the formula (VII) which may be mentionedare:

acetone, methyl ethyl ketone, methyl propyl ketone, methyl isopropylketone, methyl butyl ketone, methyl isobutyl ketone and benzaldehyde

The intermediates of the formula (VII) are known chemicals for organicsynthesis.

Formula (V) provides a general definition of the azines also required asintermediates. In formula (V), R⁴, X, Y and Z preferably, or inparticular, have those meanings which have already been mentioned abovein connection with the description of the compounds of the formula (I)according to the invention as being preferred, or particularlypreferred, for R⁴, X, Y and Z, and Q¹ preferably represents fluorine,chlorine, bromine, benzylsulphonyl or C₁ -C₄ -alkylsulphonyl, inparticular represents chlorine or methylsulphonyl.

Examples of the compounds of the formula (V) which may be mentioned are:2-chloro-, 2-benzylsulphonyl- and2-methylsulphonyl-4,6-dimethyl-pyrimidine,-4-methyl-6-methoxy-pyrimidine, -4,6-dimethoxy-pyrimidine,-4-methyl-6-ethoxy-pyrimidine, -4-chloro-6-methoxy-pyrimidine,-4-methyl-pyrimidine, -4-chloro-6-methyl-pyrimidine,-4-trifluoromethyl-6-methoxypyrimidine,-4-methoxy-6-difluoromethoxy-pyrimidine,-4-methyl-6-difluoromethoxy-pyrimidine,-4,6-bis-difluoromethoxy-pyrimidine, -4-chloro-6-ethoxy-pyrimidine,-4-chloro-6-difluoromethoxy-pyrimidine, -4-methoxy-5-methylpyrimidine,-4-trifluoromethyl-6-difluoromethoxy-pyrimidine,-4,6-diethoxy-pyrimidine, -4,5-dichloro-6-methyl-pyrimidine,-4-methyl-5-chloro-6-methoxy-pyrimidine, -4,6-dichloropyrimidine,-4-ethyl-6-methoxy-pyrimidine, -5-chloro-4,6-dimethoxy-pyrimidine,-4-methoxy-6-methylamino-pyrimidine and-4,6-bis-trifluoromethyl-pyrimidine, furthermore2-chloro-4,6-dimethyl-s-triazine,2-chloro-4-methyl-6-methoxy-s-triazine,2-chloro-4,6-dimethoxy-s-triazine, 2,4-dichloro-6-methoxy-s-triazine,2-chloro-4-ethyl-6-methoxy-s-triazine,2-chloro-4-methyl-6-ethoxy-s-triazine,2-chloro-4-ethoxy-6-methylamino-s-triazine,2-chloro-4-methoxy-6-methylamino-s-triazine,2-chloro-4-methoxy-6-ethylamino-s-triazine and2-chloro-4-ethoxy-6-ethylamino-s-triazine.

The azines of the formula (V) are known and/or can be prepared byprocesses known per se (cf., J. Chem. Soc. 1957, 1830, 1833; J. Org.Chem. 26 (1961), 792; U.S. Pat. No.3,308,119 and U.S. Pat. No.4,711,959).

Formula (X) provides a general definition of the oxadiazolones also tobe used as intermediates. In formula (X), R³ preferably, or inparticular, has the meaning which has already been mentioned above inconnection with the description of the compounds of the formula (I)according to the invention as being preferred, or particularlypreferred, for R³.

Examples of the compounds of the formula (X) which may be mentioned are:1,3,4-oxadiazol-2(3H)-one, 5-methyl-1,3,4-oxadiazol-2(3H)-one,5-ethyl-1,3,4-oxadiazol-2(3H)-one, 5-propyl-1,3,4-oxadiazol-2(3H)-one,5-isopropyl-1,3,4-oxadiazol-2(3H)-one,5-butyl-1,3,4-oxadiazol-2(3H)-one,5-trifluoromethyl-1,3,4-oxadiazol-2(3H)-one,5-tert.-butyl-1,3,4-oxadiazol-2(3H)-one,5-cyclopropyl-1,3,4-oxadiazol-2(3H)-one,5-methoxy-1,3,4-oxadiazol-2(3H)-one and5-methylthio-1,3,4-oxadiazol-2(3H)-one.

The oxadiazolones of the formula (X) are known and/or can be prepared byprocesses known per se (cf. Helv. Chim. Acta 55 (1972), 1174-1178).

Formula (III) provides a general definition of the sulphonyl halides orsulphonic anhydrides also to be used as starting substances in process(a) according to the invention for the preparation of the new compoundsof the formula (I). In formula (III), R¹ preferably, or in particular,has the meaning which has been indicated above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or particularly preferred, and Qpreferably represents chlorine.

Starting substances of the formula (III) which may be mentioned by wayof example are:

benzenesulphonyl chloride, 2-chloro-, 3-chloro-, 4-chloro-,2,5-dichloro-, 2-fluoro-, 4-fluoro-, 2-bromo-, 4-bromo-, 2-cyano-,2-nitro-, 4-nitro-, 2-methyl-, 4-methyl-, 2-chloromethyl-,2-trifluoromethyl-, 2-methoxy-, 4-methoxy-, 2-(2-methoxy-ethoxy)-,2-methylsulphonyl-, 2-isopropoxycarbonyl-, 2-chloro-6-methyl-,2-bromo-6-methyl-, 2-methylthio-, 2-trifluoromethylthio-,2-difluoromethylthio-, 2-cyclopropyloxycarbonyl-, 2-phenoxy-,2-difluoromethoxy-, 2-trifluoromethoxy-, 2-(2-chloroethoxy)-,2-methylthiomethyl-, 2-dimethylaminosulphonyl-, 2-phenyl-,2-methoxycarbonyl-, 2-ethoxycarbonyl-, 2-dimethylaminocarbonyl- and2-diethylaminocarbonyl-benzenesulphonyl chloride and (2-chloro-phenyl)-,(2-cyano-phenyl)-, (2-methoxycarbonylphenyl)-,(2-trifluoromethoxy-phenyl)- and(2-difluoromethoxy-phenyl)-methanesulphonyl chloride, furthermore1-methyl-4-methoxycarbonyl-pyrazole-5-sulphonyl chloride,1-methyl-4-ethoxycarbonyl-pyrazole-5-sulphonyl chloride,1-methyl-4-bromo-pyrazole-5-sulphonyl chloride,2-methoxycarbonyl-thiophene-3-sulphonyl chloride,3-trifluoromethyl-pyridine- 2-sulphonyl chloride,3-dimethylaminocarbonyl-pyridine-2-sulphonyl chloride,3-dimethylaminocarbonyl-6-methyl-pyridine-2-sulphonyl chloride,3-di-methylaminocarbonyl-6-chloro-pyridine-2-sulphonyl chloride and1-(iso)quinolinyl-4-ethoxycarbonyl-pyrazole-5-sulphonyl chloride.

The sulphonyl halides or sulphonic anhydrides of the formula (III) areknown and/or can be prepared by processes known per se (cf. J. Org.Chem. 33 (1968), 2104; J. Org. Chem. 25 (1960), 1824; DE-AS (GermanPublished Specification) 2,308,262; EP-OS (European PublishedSpecification) 23,140, 23,111, 23,422, 35,893, 48,143, 51,466, 64,322,70,041, 44,808 and 44,809; U.S. Pat. No. 2,929,820, 4,282,242; 4,348,220and 4,372,778 and Angew. Chem. 93 (1981), 151).

Process (a) according to the invention for the preparation of the newcompounds of the formula (I) is preferably carried out using diluents.Suitable diluents for this process are virtually all inert organicsolvents. These preferably include aliphatic and aromatic, optionallyhalogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane,petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylenechloride, ethylene chloride, chloroform, carbon tetrachloride,chlorobenzene and o-di-chlorobenzene, ethers, such as diethyl ether,dibutyl ether, glycol dimethyl ether, diglycol dimethyl ether,tetrahydrofuran and dioxane, ketones, such as acetone, methyl ethylketone, methyl isopropyl ketone and methyl isobutyl ketone, esters, suchas methyl acetate and ethyl acetate, nitriles, such as, for example,acetonitrile and propionitrile, amides, such as, for example,dimethylformamide, dimethylacetamide and N-methyl-pyrrolidone, anddimethyl sulphoxide, tetramethylene sulphone and hexamethylphosphorictriamide and pyridine.

Acid acceptors which can be employed in process (a) according to theinvention are all acid-binding agents which can customarily be used forreactions of this type. Alkali metal hydroxides, such as, for example,sodium hydroxide and potassium hydroxide, alkaline earth metalhydroxides, such as, for example, calcium hydroxide, alkali metalcarbonates and alkali metal alkoxides, such as sodium carbonate andpotassium carbonate, sodium tert.-butoxide and potassium tert.-butoxide,furthermore aliphatic, aromatic or heterocyclic amines, for exampletriethylamine, trimethylamine, dimethylaniline, dimethylbenzylamine,pyridine, picoline, 1,5-diazabicyclo-[4,3,0]-non-5-ene (DBN),1,8-diazabicyclo-[5,4,0]-undec-7-ene (DBU) and1,4-diazabicyclo-[2,2,2]-octane (DABCO), are preferably suitable.

In process (a) according to the invention, the reaction temperatures canbe varied within a relatively wide range. In general, the reaction iscarried out at temperatures between -50° C. and +50° C., preferably attemperatures between -40° C. and +40° C.

For carrying out process (a) according to the invention, between 1 and 5moles, preferably between 1 and 4 moles, of sulphonyl halide orsulphonic anhydride of the formula (III) are generally employed per moleof aminotriazolinone of the formula (II). In the case wheredisulphonylated compounds of the formula (I, R² =--SO₂ --R¹) are to beprepared in a one-pot reaction, at least 2 moles of sulphonyl halide orsulphonic anhydride (III) are to be employed per mole ofaminotriazolinone (II).

The reactants can be combined in any desired sequence. In a preferredembodiment of process (a) according to the invention, the startingsubstances of the formula (II) and (III) are stirred at room temperaturewith a diluent, and the acid acceptor is slowly metered into thismixture, if appropriate after cooling. The reaction mixture is thenstirred until the reaction is complete.

Working up can be carried out in a customary manner, for example bywashing with water--if appropriate after concentrating and/or dilutingthe mixture with a virtually water-immiscible organic solvent, such as,for example, methylene chloride -, drying and filtering the mixture, andcarefully distilling off the solvent from the filtrate. The crudeproduct, which remains in the residue, can be purified further in acustomary manner, for example by column chromatography and/or byrecrystallization.

The compounds which can be obtained as described above of the formula(I) in which R² represents the group --SO₂ --R¹ can be reacted to givecompounds of the formula (I) in which R² represents hydrogen by reactionwith desulphonylating agents, if appropriate in the presence ofdiluents.

In this connection, desulphonylating agents are taken to mean substanceswhich can eliminate a sulphonyl group from N,N-bis-sulphonyl-aminocompounds. Suitable desulphonylating agents are above all alkali metalhydroxides or alkaline earth metal hydroxides, such as sodium hydroxide,potassium hydroxide and calcium hydroxide, alkali metal alkoxides, suchas sodium methoxide, potassium methoxide, sodium ethoxide and potassiumethoxide, furthermore ammonia, alkylamines, such as methylamine,ethylamine, propylamine and butylamine, and also dialkylamines, such asdimethylamine and diethylamine. It is preferred to employ ammonia as thedesulphonylating agent.

The desulphonylation is preferably carried out in the presence ofdiluents. Preferred diluents, besides water, are polar organic solvents,such as methanol, ethanol, propanol, isopropanol, 2-methoxyethanol,2-ethoxy-ethanol and dioxane.

The desulphonylation is generally carried out at temperatures between 0°C. and 150° C., preferably at temperatures between 20° C. and 100° C.

In general, the reactants for desulphonylation are mixed at roomtemperature and stirred until the reaction is complete, if appropriateat increased temperature. For working up, the mixture is concentrated,if appropriate, diluted with water, and acidified using a strong acid,such as, for example, hydrochloric acid. The product, which is obtainedin this process in the form of crystals (I, R² =H), can be isolated byfiltering off with suction.

If desired, salts can be prepared from the compounds of the generalformula (I) according to the invention. Such salts are obtained in asimple manner by customary salt formation methods, for example bydissolving or dispersing a compound of the formula (I) in a suitablesolvent, such as, for example, water, methanol, ethanol or acetone, andadding a suitable acid or base. The salts can then be isolated byconcentration or filtering off with suction, if appropriate afterstirring for some time.

Formula (IV) provides a general definition of thesulphonylaminotriazolinones to be used as starting substances in process(b) according to the invention for the preparation of compounds of theformula (I).

In formula (IV), R¹, R² and R³ preferably, or in particular, have themeanings which have already been indicated above in connection with thedescription of the compounds of the formula (I) according to theinvention as being preferred, or particularly preferred, for R¹, R² andR³.

Starting substances of the formula (IV) which may be mentioned by way ofexample are:

4-(phenylsulphonylamino)-, 4-(2-chloro-phenylsulphonylamino)-4-(2-fluoro-phenylsulphonylamino)-, 4-(2-bromophenylsulphonylamino)-,4-(2-methyl-phenylsulphonylamino)-, 4-(2-methoxy-phenylsulphonylamino)-,4-(2-trifluoromethyl-phenylsulphonylamino)-,4-(2-methylthio-phenylsulphonylamino)-,4-(2-methylsulphonyl-phenylsulphonylamino)-,4-(2-isopropoxycarbonyl-phenylsulphonylamino)-,4-(2-chloro-6-methylphenylsulphonylamino)-,4-(2-phenyl-phenylsulphonylamino)-,4-(2-difluoromethoxy-phenylsulphonylamino)-,4-(2-trifluoromethoxy-phenylsulphonylamino)-,4-(2-dimethylaminosulphonylphenylsulphonylamino)-,4-(2-methoxycarbonyl-phenylsulphonylamino)-,4-(2-ethoxycarbonyl-phenylsulphonylamino)-,4-(2-chloro-phenylmethyl-sulphonylamino)-,4-(2-methoxycarbonyl-phenylmethylsulphonylamino)-,4-(2-ethoxycarbonylphenylmethylsulphonylamino)-,4-(2-difluoromethoxy-phenylmethylsulphonylamino)-,4-(2-trifluoromethoxy-phenylmethylsulphonylamino)-,4-(1-methyl-4-methoxycarbonyl-pyrazol-5-yl-sulphonylamino)-,4-(1-methyl-4-ethoxycarbonyl-pyrazol-5-yl-sulphonylamino)-,4-(1-methyl-4-bromo-pyrazol-5-yl-sulphonylamino)-,4-(2-methoxycarbonyl-thiophen-3-yl-sulphonylamino)-,4-(3-trifluoromethyl-pyridin-2-yl-sulphonylamino)-,4-(3-dimethylaminocarbonyl-pyridin-2-yl-sulphonylamino)- and4-(1-isoquinolinyl-4-ethoxycarbonyl-pyrazol-5-yl-sulphonylamino)-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-ethyl-2,4-dihydro3H-1,2,4-triazol-3-one,-5-propyl-2,4-dihydro-3H-1,2,4-triazol-3 -one,-5-isopropyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-trifluoromethyl-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one,-5-t-butyl-2,4-dihydro-3H,1,2,4-triazol-3-one, -5-benzyl-2,4-dihydro-3H-1,2,4-triazol-3-one and -5-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-one.

The sulphonylaminotriazolinones of the formula (IV) to be used asstarting substances were hitherto unknown from the literature. The newcompounds of the formula (IV) are obtained when aminotriazolinones ofthe general formula (VI) ##STR52## in which R³ has the above-mentionedmeaning, are reacted with sulphonyl halides or sulphonic anhydrides ofthe general formula (III) ##STR53## in which R¹ and Q have theabove-mentioned meanings,

if appropriate, the presence of an acid acceptor, such as, for example,triethylamine, pyridine or 1,4-diazabicyclo-[2,2,2]-octane (DABCO), and,if appropriate, in the presence of a diluent, such as, for example,methylene chloride, tetrahydrofuran or dioxane, at temperatures between-50° C. and +50° C.

As far as the starting substances of the formulae (III) and (VI) areconcerned, the instructions indicated above in the description ofprocess (a) according to the invention, relating to these substances,are also true in this connection.

As far as the azines of the formula (V) are concerned, which are to beused as starting substances in process (b) according to the invention,the instructions indicated above in the description of process (a)according to the invention are also true in this connection.

Process (b) according to the invention is preferably carried out usingdiluents. Suitable solvents are those which have been indicated above asdiluents in process (a).

Process (b) is preferably carried out in the presence of an acidacceptor. Suitable acid acceptors are the same acid-binding agents whichhave been indicated above in process (a).

In process (b) according to the invention, the reaction temperatures canbe varied within a relatively wide range. In general, the process iscarried out at temperatures between 0° C. and +150° C., preferably attemperatures between +20° C. and +120° C.

Process (b) according to the invention is generally carried out underatmospheric pressure. However, it is also possible to carry out theprocess under increased or reduced pressure.

For carrying out process (b) according to the invention, the startingsubstances required in each case are generally employed in approximatelyequimolar amounts. However, it is also possible to use one of the twocomponents employed in each case in a relatively large excess. Thereactions are generally carried out in a suitable diluent in thepresence of an acid acceptor, and the reaction mixture is stirred forseveral hours at the specific temperature required. Working-up inprocess (b) according to the invention is carried out in each case bycustomary methods.

The active compounds according to the invention can be used asdefoliants, desiccants, agents for destroying broad-leaved plants and,especially, as weedkillers. By weeds, in the broadest sense, there areto be understood all plants which grow in locations where they areundesired. Whether the substances according to the invention act astotal or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can be used, forexample, in connection with the following plants: Dicotyledon weeds ofthe genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis,Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca,Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium,Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica,Abutilon, Emex, Datura, Viola, Galeopsis, Papaver and Centaurea.

Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus,Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana,Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum,Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus,Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis,Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea,Dactyloctenium, Agrostis, Alopecurus and Apera.

Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum,Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus andAllium.

However, the use of the active compounds according to the invention isin no way restricted to these genera, but also extends in the samemanner to other plants.

The compounds are suitable, depending on the concentration, for thetotal combating of weeds, for example on industrial terrain and railtracks, and on paths and squares with or without tree plantings.Equally, the compounds can be employed for combating weeds in perennialcultures, for example afforestations, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hopfields, andfor the selective combating of weeds in annual cultures.

The compounds of the formula (I) according to the invention areparticularly suitable for selectively combating dicotyledon weeds inmonocotyledon crops, above all using the post-emergence method.

The active compounds can be converted to the customary formulations,such as solutions, emulsions, wettable powders, suspensions, powders,dusting agents, pastes, soluble powders, granules, suspension-emulsionconcentrates, natural and synthetic materials impregnated with activecompound, and very fine capsules in polymeric substances.

These formulations are produced in known manner, for example by mixingthe active compounds with extenders, that is liquid solvents and/orsolid carriers, optionally with the use of surface-active agents, thatis emulsifying agents and/or dispersing agents and/or foam-formingagents.

In the case of the use of water as an extender, organic solvents can,for example, also be used as auxiliary solvents. As liquid solvents,there are suitable in the rain: aromatics, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics and chlorinated aliphatichydrocarbons, such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, forexample petroleum fractions, mineral and vegetable oils, alcohols, suchas butanol or glycol as well as their ethers and esters, ketones, suchas acetone, methyl ethyl ketone, methyl isobutyl ketone orcyclohexanon:, strongly polar solvents, such as dimethylformamide anddimethyl sulphoxide, as well as water.

As solid carriers there are suitable: for example ammonium salts andground natural minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as highly disperse silica, alumina and silicates, assolid carriers for granules there are suitable: for example crushed andfractionated natural rocks such as calcite, marble, pumice, sepioliteand dolomite, as well as synthetic granules of inorganic and organicmeals, and granules of organic material such as sawdust, coconut shells,corn cobs and tobacco stalks; as emulsifying and/or foam-forming agentsthere are suitable: for example non-ionic and anionic emulsifiers, suchas polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkylsulphates, arylsulphonates as well as albumin hydrolysis products; asdispersing agents there are suitable: for example lignin-sulphite wasteliquors and methylcellulose. Adhesives such as carboxymethylcelluloseand natural and synthetic polymers in the form of powders, granules orlatices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, aswell as natural phospholipids, such as cephalins and lecithins, andsynthetic phospholipids, can be used in the formulations. Furtheradditives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic dyestuffs,such as alizarin dyestuffs, azo dyestuffs and metal phthalocyaninedyestuffs, and trace nutrients such as salts of iron, manganese, boron,copper, cobalt, molybdenum and zinc.

The formulations in general contain between 0.1 and 95 per cent byweight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in the formof their formulations, can also be used, for combating weeds, asmixtures with known herbicides, finished formulations or tank mixesbeing possible.

Suitable herbicides for the mixtures are known herbicides, such as, forexample,1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(1H,3H)-dione(AMETHYDIONE) or N-(2-benzothiazolyl)-N,N'-dimethylurea(METABENZTHIAZURON) for combating weeds in cereals;4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) forcombating weeds in sugar beets, and4-amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one(METRIBUZIN) for combating weeds in soy beans; 2,4-dichlorophenoxyaceticacid (2,4-D); 4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB);2,4-dichlorophenoxypropionic acid (2,4-DP);3-isopropyl-2,1,3-bensothiadiazin-4-one 2,2-dioxide (BENTAZONE); methyl5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX);3,5-dibromo-4-hydroxy-benzonitrile (BROMOXYNIL);2-chloro-N-{[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}benzenesulphonamide(CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methylphenyl)-urea(CHLORTOLURON); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, itsmethyl ester or its ethyl ester (DICLOFOP);2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methylester or its ethyl ester (FENOXAPROP);[(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its1-methylheptyl ester (FLUROXYPYR); methyl2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-4(5)-methylbenzoate(IMAZAMETHABENZ); 3,5-diodo-4-hydroxybenzonitrile (IOXYNIL);N,N-dimethyl-N'-(4-isopropylphenyl)-urea (ISOPROTURON);(2-methyl-4-chlorophenoxy)-acetic acid (MCPA);(4-chloro-2-methylphenoxy)-propionic acid (MCPP);N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET);2-{[[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)amino)-carbonyl]-amino]-sulphonyl}-benzoicacid or its methyl ester (METSULFURON);N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN);0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE);2-[1-(ethoxamino)-butylidene]-5-(2-ethylthiopropyl)-1,3-cyclohexadione(SETHOXYDIM); 4-ethylamino-2-t-butylamino- 6-methylthio-s-triazine(TERBUTRYNE) and methyl3-[[[[4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl]amino]-sulphonyl]-thiophene-2-carboxylate(THIAMETURON). Surprisingly, some mixtures also show synergistic action.

Mixtures with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents plant nutrientsand agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in the customary manner, for example bywatering, spraying, atomizing or scattering.

The active compounds according to the invention can be applied eitherbefore or after emergence of the plants.

They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range.It depends essentially on the nature of the desired effect. In general,the amounts used are between 0.01 and 10 kg of active compound perhectare of soil surface, preferably between 0.05 and 5 kg per ha.

The preparation and use of the active compounds according to theinvention can be seen from the following examples.

PREPARATION EXAMPLES EXAMPLE 1 ##STR54## (Process (a))

A mixture of 7.2 g (0.03 mol) of4-amino-2-(4,6-dimethoxypyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one,21.0 g (0.09 mol) of 2-methoxycarbonyl-benzenesulphonyl chloride and 50ml of pyridine is stirred at 20° C. for 12 hours. The mixture issubsequently concentrated under a waterpump vacuum, and the residue istaken up in methylene chloride and washed with 2N hydrochloric acid. Themixture is dried using magnesium sulphate and then filtered, and thesolvent is carefully distilled off from the filtrate under a waterpumpvacuum.

12.0 g (63% of theory) of4-[bis-(2-methoxycarbonylphenylsulphonyl)-amino]-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained as a crystalline residue of melting point 176° C.

EXAMPLE 2 ##STR55##

A mixture of 6.4 g (0.01 mol) of4-[bis-(2-methoxycarbonyl-phenylsulphonyl)-amino]-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one(cf. Example 1), 100 ml of methanol and 10 ml of concentrated aqueousammonia is stirred at 50° C. for 60 minutes. The mixture is subsequentlyconcentrated under a waterpump vacuum, and the residue is taken up inwater and acidified using 2N hydrochloric acid. The product which isobtained in this process in the form of crystals is isolated byfiltering off with suction.

4.0 g (92% of theory) of4-(2-methoxycarbonyl-phenylsulphonylamino)-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 192° C. are obtained.

EXAMPLE 3 ##STR56## (Process (a))

A mixture of 4.2 g (0.016 mol) of4-amino-5-methyl-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one,11.7 g (0.05 mol) of 2-methoxycarbonylbenzenesulphonyl chloride and 50ml of pyridine is stirred at 20° C. for 12 hours, then diluted withice-water and acidified using 2N hydrochloric acid, and the mixture isshaken with methylene chloride. The organic phase is separated off,dried using magnesium sulphate and filtered. The solvent is carefullydistilled off from the filtrate under a waterpump vacuum.

3.8 g (50% of theory) of4-(2-methoxycarbonyl-phenylsulphonylamino)-5-methyl-2-(4,6-dimethoxy-pyrimidin-2yl)2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained as a crystalline residue of melting point 174° C.

EXAMPLE 4 ##STR57## (Process (a))

A mixture of 5.7 g (0.02 mol) of4-amino-5-methylthio-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one,14.0 g (0.06 mol) of 2-methoxycarbonylbenzenesulphonyl chloride and 50ml of pyridine is stirred at 20° C. for 48 hours. The mixture issubsequently concentrated under a waterpump vacuum, the residue is takenup in methylene chloride, and the mixture is washed using 2Nhydrochloric acid, dried using magnesium sulphate and filtered. Thefiltrate is concentrated and the residue is purified by columnchromatography on silica gel using methylene chloride/methanol (vol.10:1).

3.0 g (31% of theory) of4-(2-methoxycarbonyl-phenylsulphonylamino)-5-methylthio-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 179° C. are obtained.

The compounds of the formula (I) which are listed in Table 2 below canbe prepared analogously to Examples 1 to 4 and in accordance with thegeneral description of the process according to the invention. ##STR58##

                                      TABLE 2                                     __________________________________________________________________________    Examples of the compounds of the formula (I)                                  Ex-                                                                           am-                                                       Melting             ple                                                       point               No.                                                                              R.sup.1         R.sup.2      R.sup.3 R.sup.4                                                                            X  Y  Z      (°C.)        __________________________________________________________________________                       H            H       SO.sub.2 CH.sub.3                                                                  N  CH COCH.sub.3                                                                           191                 6                                                                                 ##STR59##      H            CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                  N  CH COCH.sub.3                                                                           140                 7                                                                                 ##STR60##      H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           178                 8                                                                                 ##STR61##      H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           186                 9                                                                                 ##STR62##                                                                                     ##STR63##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  10                                                                                ##STR64##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  11                                                                                ##STR65##      Na           H       CH.sub.3                                                                           N  CH CCH.sub.3                  12                                                                                ##STR66##                                                                                     ##STR67##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  13                                                                                ##STR68##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  14                                                                                ##STR69##                                                                                     ##STR70##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  15                                                                                ##STR71##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  16                                                                                ##STR72##                                                                                     ##STR73##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  17                                                                                ##STR74##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  18                                                                                ##STR75##                                                                                     ##STR76##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  19                                                                                ##STR77##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  20                                                                                ##STR78##                                                                                     ##STR79##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  21                                                                                ##STR80##                                                                                     ##STR81##   H       CH.sub.3                                                                           N  N  CCH.sub.3                  22                                                                                ##STR82##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  23                                                                                ##STR83##                                                                                     ##STR84##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  24                                                                                ##STR85##                                                                                     ##STR86##   H       CH.sub.3                                                                           N  CH CCH.sub.3                  25                                                                                ##STR87##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  26                                                                                ##STR88##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  27                                                                                ##STR89##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  28                                                                                ##STR90##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  29                                                                                ##STR91##      H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  30                                                                                ##STR92##                                                                                     ##STR93##   H       CH.sub.3                                                                           N  CH COCH.sub.3                 31                                                                                ##STR94##      H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 32                                                                                ##STR95##                                                                                     ##STR96##   H       CH.sub.3                                                                           N  CH COCH.sub.3                 33                                                                                ##STR97##      H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 34                                                                                ##STR98##                                                                                     ##STR99##   H       CH.sub.3                                                                           N  CH COCH.sub.3                 35                                                                                ##STR100##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 36                                                                                ##STR101##     H            H       CH.sub.3                                                                           N  CH COCH.sub.                                                                            181                 37                                                                                ##STR102##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 38                                                                                ##STR103##                                                                                    ##STR104##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 39                                                                                ##STR105##                                                                                    ##STR106##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 40                                                                                ##STR107##                                                                                    ##STR108##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 41                                                                                ##STR109##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 42                                                                                ##STR110##                                                                                    ##STR111##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 43                                                                                ##STR112##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 44                                                                                ##STR113##                                                                                    ##STR114##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 45                                                                                ##STR115##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 46                                                                                ##STR116##                                                                                    ##STR117##  H       CH.sub.3                                                                           N  CH COCH.sub.3                 47                                                                                ##STR118##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                                                                           219                 48                                                                                ##STR119##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 49                                                                                ##STR120##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 50                                                                                ##STR121##     H            H       CH.sub.3                                                                           N  CH COCH.sub.3                 51                                                                                ##STR122##                                                                                    ##STR123##  H       CH.sub.3                                                                           N  CH CCH.sub.3                  52                                                                                ##STR124##     H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  53                                                                                ##STR125##                                                                                    ##STR126##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 54                                                                                ##STR127##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 55                                                                                ##STR128##                                                                                    ##STR129##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 56                                                                                ##STR130##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 57                                                                                ##STR131##                                                                                    ##STR132##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 58                                                                                ##STR133##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 59                                                                                ##STR134##                                                                                    ##STR135##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 60                                                                                ##STR136##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 61                                                                                ##STR137##                                                                                    ##STR138##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 62                                                                                ##STR139##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 63                                                                                ##STR140##                                                                                    ##STR141##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 64                                                                                ##STR142##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 65                                                                                ##STR143##                                                                                    ##STR144##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 66                                                                                ##STR145##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 67                                                                                ##STR146##                                                                                    ##STR147##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 68                                                                                ##STR148##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           208                 69                                                                                ##STR149##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 70                                                                                ##STR150##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 71                                                                                ##STR151##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 72                                                                                ##STR152##                                                                                    ##STR153##  H       CF.sub.3                                                                           N  CH COCH.sub.3                 73                                                                                ##STR154##                                                                                    ##STR155##  H       OCH.sub.3                                                                          N  CH CCl                        74                                                                                ##STR156##     H            H       CF.sub.3                                                                           N  CH COCH.sub.3                 75                                                                                ##STR157##                                                                                    ##STR158##  H       CF.sub.3                                                                           N  CH COCH.sub.3                 76                                                                                ##STR159##     H            H       CF.sub.3                                                                           N  CH COCH.sub.3                 77                                                                                ##STR160##     H            H       CF.sub.3                                                                           N  CH COCH.sub.3                 78                                                                                ##STR161##     H            H       OCH.sub.3                                                                          N  CH CCl                        79                                                                                ##STR162##                                                                                    ##STR163##  H       OCH.sub.3                                                                          N  CH CCl                        80                                                                                ##STR164##     H            H       OCH.sub.3                                                                          N  CH CCl                        81                                                                                ##STR165##     H            H       OCH.sub.3                                                                          N  CH CCl                        82                                                                                ##STR166##                                                                                    ##STR167##  H       OCH.sub.3                                                                          N  CH CCl                        83                                                                                ##STR168##                                                                                    ##STR169##  H       OCH.sub.3                                                                          N  CH CCl                        84                                                                                ##STR170##     H            H       OCH.sub.3                                                                          N  CH CCl                        85                                                                                ##STR171##                                                                                    ##STR172##  H       OCH.sub. 3                                                                         N  CH COCHF.sub.2                86                                                                                ##STR173##     H            H       OCH.sub.3                                                                          N  CH COCHF.sub.2                87                                                                                ##STR174##                                                                                    ##STR175##  H       OCH.sub.3                                                                          N  CH COCHF.sub.2                88                                                                                ##STR176##     H            H       OCH.sub.3                                                                          N  CH COCHF.sub.2                89                                                                                ##STR177##                                                                                    ##STR178##  H       OCH.sub.3                                                                          N  CH COCHF.sub.2                90                                                                                ##STR179##     H            H       OCH.sub.3                                                                          N  CH COCHF.sub.2                91                                                                                ##STR180##                                                                                    ##STR181##  H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                                                                          198                 92                                                                                ##STR182##     H            H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                                                                          180                 93                                                                                ##STR183##                                                                                    ##STR184##  H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                94                                                                                ##STR185##     H            H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                95                                                                                ##STR186##                                                                                    ##STR187##  H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                96                                                                                ##STR188##     H            H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                97                                                                                ##STR189##                                                                                    ##STR190##  H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                98                                                                                ##STR191##     H            H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                99                                                                                ##STR192##                                                                                    ##STR193##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 100                                                                               ##STR194##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 101                                                                               ##STR195##                                                                                    ##STR196##  H       OCH.sub.3                                                                          N  CH CCl                        102                                                                               ##STR197##     H            H       OCH.sub.3                                                                          N  CH CCl                        103                                                                               ##STR198##                                                                                    ##STR199##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 104                                                                               ##STR200##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 105                                                                               ##STR201##                                                                                    ##STR202##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 106                                                                               ##STR203##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 107                                                                               ##STR204##                                                                                    ##STR205##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 108                                                                               ##STR206##                                                                                    ##STR207##  H       OCH.sub.3                                                                          N  CH COCHF.sub.2                109                                                                               ##STR208##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 110                                                                               ##STR209##                                                                                    ##STR210##  H       OCH.sub.3                                                                          N  CH COCHF.sub.2                111                                                                               ##STR211##     H            H       CH.sub.3                                                                           N  N  CCH.sub.3                  112                                                                               ##STR212##                                                                                    ##STR213##  H       CH.sub.3                                                                           N  N  CCH.sub.3                  113                                                                               ##STR214##                                                                                    ##STR215##  H       CH.sub.3                                                                           N  N  CCH.sub.3                  114                                                                               ##STR216##                                                                                    ##STR217##  H       CH.sub.3                                                                           N  N  COCH.sub.3                 115                                                                               ##STR218##     H            H       CH.sub.3                                                                           N  N  COCH.sub.3                 116                                                                               ##STR219##                                                                                    ##STR220##  H       CH.sub.3                                                                           N  N  COCH.sub.3                 117                                                                               ##STR221##     H            H       CH.sub.3                                                                           N  N  COCH.sub.3                 118                                                                               ##STR222##                                                                                    ##STR223##  H       CH.sub.3                                                                           N  N  COCH.sub.3                 119                                                                               ##STR224##     H            H       CH.sub.3                                                                           N  N  COCH.sub.3                 120                                                                               ##STR225##     Na           H       CH.sub.3                                                                           N  N  COCH.sub.3                 121                                                                               ##STR226##                                                                                    ##STR227##  H       CH.sub.3                                                                           N  N  COCH.sub.3                 122                                                                               ##STR228##     H            H       CH.sub.3                                                                           N  N  COCH.sub.3                 123                                                                               ##STR229##                                                                                    ##STR230##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 124                                                                               ##STR231##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 125                                                                               ##STR232##                                                                                    ##STR233##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 126                                                                               ##STR234##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 127                                                                               ##STR235##                                                                                    ##STR236##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 128                                                                               ##STR237##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 129                                                                               ##STR238##                                                                                    ##STR239##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 130                                                                               ##STR240##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 131                                                                               ##STR241##                                                                                    ##STR242##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 132                                                                               ##STR243##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 133                                                                               ##STR244##                                                                                    ##STR245##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 134                                                                               ##STR246##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 135                                                                               ##STR247##                                                                                    ##STR248##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 136                                                                               ##STR249##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 137                                                                               ##STR250##                                                                                    ##STR251##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 138                                                                               ##STR252##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 139                                                                               ##STR253##                                                                                    ##STR254##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 140                                                                               ##STR255##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                                                                           201                 141                                                                               ##STR256##                                                                                    ##STR257##  H       OCHF.sub.2                                                                         N  CH COCHF.sub.2                142                                                                               ##STR258##                                                                                    ##STR259##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 143                                                                               ##STR260##                                                                                    ##STR261##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 144                                                                               ##STR262##                                                                                    ##STR263##  H       CH.sub.3                                                                           N  N  CCH.sub.3                  145                                                                               ##STR264##     H            H       CH.sub.3                                                                           N  N  CCH.sub.3                  146                                                                               ##STR265##                                                                                    ##STR266##  H       CH.sub.3                                                                           N  N  CCH.sub.3                  147                                                                               ##STR267##                                                                                    ##STR268##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 148                                                                               ##STR269##                                                                                    ##STR270##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 149                                                                               ##STR271##                                                                                    ##STR272##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 150                                                                               ##STR273##                                                                                    ##STR274##  H       OCH.sub.3                                                                          N  N  CCl                        151                                                                               ##STR275##                                                                                    ##STR276##  H       C.sub.2 H.sub.5                                                                    N  N  COCH.sub.3                 152                                                                               ##STR277##                                                                                    ##STR278##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 153                                                                               ##STR279##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 154                                                                               ##STR280##     H            H       OCH.sub.3                                                                          N  N  CCH.sub.3                  155                                                                               ##STR281##                                                                                    ##STR282##  H       OCH.sub.3                                                                          N  N  CNHC.sub.2 H.sub.5         156                                                                               ##STR283##                                                                                    ##STR284##  H       OC.sub.2 H.sub.5                                                                   N  N  CNHCH.sub.3                157                                                                               ##STR285##                                                                                    ##STR286##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 158                                                                               ##STR287##                                                                                    ##STR288##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 159                                                                               ##STR289##                                                                                    ##STR290##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 160                                                                               ##STR291##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 161                                                                               ##STR292##                                                                                    ##STR293##  H       OCH.sub.3                                                                          N  CH COCH.sub.3                 162                                                                               ##STR294##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 163                                                                               ##STR295##                                                                                    ##STR296##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 164                                                                               ##STR297##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 165                                                                               ##STR298##                                                                                    ##STR299##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 166                                                                               ##STR300##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 167                                                                               ##STR301##                                                                                    ##STR302##  H       OCH.sub.3                                                                          N  N  COCH.sub.3                 168                                                                               ##STR303##                                                                                    ##STR304##  H       CH.sub.3                                                                           N  CH CCH.sub.3                  169                                                                               ##STR305##     H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  170                                                                               ##STR306##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 171                                                                               ##STR307##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 172                                                                               ##STR308##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 173                                                                               ##STR309##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 174                                                                               ##STR310##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 175                                                                               ##STR311##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 176                                                                               ##STR312##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 177                                                                               ##STR313##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 178                                                                               ##STR314##     H            H       OCH.sub.3                                                                          N  N  COCH.sub.3                 179                                                                               ##STR315##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                                                                            233                 180                                                                               ##STR316##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                  181                                                                               ##STR317##     H            SCH.sub.3                                                                             CH.sub.3                                                                           N  CH CCH.sub.3                  182                                                                               ##STR318##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                  183                                                                               ##STR319##     H            SCH.sub.3                                                                             OCH.sub.3                                                                          N  CH COCH.sub.3                 184                                                                               ##STR320##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  COCH.sub.3                 185                                                                               ##STR321##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  N  COCH.sub.3                 186                                                                               ##STR322##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  N  COCH.sub.3                 187                                                                               ##STR323##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  C OCH.sub.3                                                                          202                 188                                                                               ##STR324##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH CCl                        189                                                                               ##STR325##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                 190                                                                               ##STR326##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  COCH.sub.3                 191                                                                               ##STR327##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  N  COCH.sub.3                 192                                                                               ##STR328##                                                                                    ##STR329##  H       CH.sub.3                                                                           N  CH CCH.sub.3                  193                                                                               ##STR330##     H            H       CH.sub.3                                                                           N  CH CCH.sub.3                  194                                                                               ##STR331##     H            SCH.sub.3                                                                             CH.sub.3                                                                           N  N  COCH.sub.3                 195                                                                               ##STR332##     H            SCH.sub.3                                                                             CH.sub.3                                                                           N  N  COCH.sub.3                 196                                                                               ##STR333##     H            SCH.sub.3                                                                             OCH.sub.3                                                                          N  N  COCH.sub.3                 197                                                                               ##STR334##     H            H       SO.sub.2 CH.sub.3                                                                  CH N  COCH.sub.3                 198                                                                               ##STR335##     H            CH.sub.3                                                                              SO.sub.2 CH.sub.3                                                                  CH N  COCH.sub.3                 199                                                                               ##STR336##                                                                                    ##STR337##  CH.sub.3                                                                              OCHF.sub.2                                                                         CH N  COCHF.sub.2                                                                          200                 200                                                                               ##STR338##                                                                                    ##STR339##  C.sub.2 H.sub.5                                                                       CH.sub.3                                                                           N  N  COCH.sub.3                 201                                                                               ##STR340##     H            CH(CH.sub.3 ).sub.2                                                                   OCH.sub.3                                                                          N  CH COCH.sub.3                 202                                                                               ##STR341##     H            CH.sub.2 CH(CH.sub.3).sub.2                                                           OCH.sub.3                                                                          N  N  COCH.sub.3                 203                                                                               ##STR342##     H            C(CH.sub.3).sub.3                                                                     CH.sub.3                                                                           N  CH COCH.sub.3                 204                                                                               ##STR343##     H            C(CH.sub.3).sub.3                                                                     OCH.sub.3                                                                          N  CH COCH.sub.3                 205                                                                               ##STR344##     H            CF.sub.3                                                                              CH.sub.3                                                                           N  N  COCH.sub.3                 206                                                                               ##STR345##     H            CH.sub.3                                                                              OCHF.sub.2                                                                         N  CH COCHF.sub.2                                                                          118                 207                                                                               ##STR346##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           198                 208                                                                               ##STR347##     H            C.sub.2 H.sub.5                                                                       OCH.sub.3                                                                          N  CH C OCH.sub.3                                                                          174                 209                                                                               ##STR348##                                                                                    ##STR349##  CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           204                 210                                                                               ##STR350##     H            C.sub.3 H.sub.7                                                                       OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           179                 211                                                                               ##STR351##                                                                                    ##STR352##  CH(CH.sub.3).sub.2                                                                    OCH.sub.3                                                                          N  CH COCH.sub.3                                                                           184                 212                                                                               ##STR353##                                                                                    ##STR354##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 213                                                                               ##STR355##                                                                                    ##STR356##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 214                                                                               ##STR357##                                                                                    ##STR358##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 215                                                                               ##STR359##                                                                                    ##STR360##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 216                                                                               ##STR361##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 217                                                                               ##STR362##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                                                                           232                 218                                                                               ##STR363##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                                                                           247                 219                                                                               ##STR364##                                                                                    ##STR365##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                                                                           203                 220                                                                               ##STR366##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                 221                                                                               ##STR367##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH COCH.sub.3                                                                           248                 222                                                                               ##STR368##                                                                                    ##STR369##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                                                                            206                 223                                                                               ##STR370##     H            CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                                                                            308                 224                                                                               ##STR371##                                                                                    ##STR372##  CH.sub.3                                                                              CH.sub.3                                                                           N  CH CCH.sub.3                                                                            195                 225                                                                               ##STR373##     H            H       OCH.sub.3                                                                          N  CH COCH.sub.3                 226                                                                               ##STR374##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                 227                                                                               ##STR375##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  CH COCH.sub.3                 228                                                                               ##STR376##     H            SCH.sub.3                                                                             OCH.sub.3                                                                          N  CH COCH.sub.3                 229                                                                               ##STR377##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  COCH.sub.3                                                                           179                 230                                                                               ##STR378##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  COCH.sub.3                                                                           (amor- phous)       231                                                                               ##STR379##     H            CH.sub.3                                                                              OCH.sub.3                                                                          N  N  COCH.sub.3                                                                           87                  __________________________________________________________________________

The preparation in accordance with process (b) of the compound listed asExample No. 221 in Table 2 is described below by way of example:##STR380##

(process (b))

A mixture of 23.1 g (0.070 mol) of4-(2-trifluoromethoxyphenylsulphonylamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,14.5 g (0.072 mol) of 4-methoxy-6-methyl-2-methylsulphonyl-pyrimidine,50 g of potassium carbonate and 300 ml dioxane is refluxed for 6 hours.The mixture is allowed to cool and then filtered, the filter residue iswashed with water and then taken up in methylene chloride and 5%strength hydrochloric acid, and the mixture is shaken. The organic phaseis dried using sodium sulphate and filtered. After the filtrate has beenconcentrated, the residue is made to crystallize by trituration withethanol, and the crystalline product is isolated by filtering off withsuction.

6.0 g (21% of theory) of4-(2-trifluoromethoxy-phenylsulphonylamino)-5-methyl-2-(4-methoxy-6-methylpyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 248° C. are obtained.

Starting substances of the formula (II) EXAMPLE (II-1) ##STR381##

A mixture of 7.0 g (0.05 mol) of 4-(1-methyl-ethylideneamino)-24-dihydro-3H-1,2,4-triazol-3-one, 21 g (0.15 mol) of potassiumcarbonate, 11.0 g (0.05 mol) of4,6-dimethoxy2-methylsulphonyl-pyrimidine and 100 ml of acetonitrile isrefluxed for 3 hours. After the mixture has cooled, it is filtered andthe filtrate is concentrated, the residue is taken up in 100 ml ofethanol/water (vol. 1:1), and the mixture is stirred for 3 hours at 60°C. after 1 ml of concentrated hydrochloric acid has been added. Themixture is concentrated, the residue is then triturated with ethanol,and the product obtained in the form of crystals is isolated byfiltering off with suction. 9.7 g (82% of theory) of4-amino-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 238° C. are obtained.

EXAMPLE (II-2) ##STR382##

A mixture of 4.0 g (0.02 mol) of4-(1,3-dimethylbutylideneamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one,8.3 g (0.06 mol) of potassium carbonate, 4.4 g (0.02 mol) of4,6-dimethoxy-2-methylsulphonyl-pyrimidine and 100 ml of acetonitrile isrefluxed for 3 hours. After the mixture has cooled it is filtered, thefiltrate is concentrated, the residue is taken up in 100 ml ofethanol/water (vol. 1:1) and stirred for 60 minutes at 60° C. after 2drops of concentrated hydrochloric acid have been added. The mixture isconcentrated, the residue is stirred with saturated sodium hydrogencarbonate solution, and the crystalline product is isolated by filteringoff with suction.

2.6 g (52% of theory) of4-amino-5-methyl-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 219° C. are obtained.

EXAMPLE (II-3) ##STR383##

A mixture of 3.0 g (0.02 mol) of4-amino-5-methylthio-2,4-dihydro-3H-1,2,4-triazol-3-one and 200 ml ofacetone is refluxed for 4 hours after 0.1 g of p-toluenesulphonic acidhas been added. The mixture is concentrated, the residue is taken up in100 ml of acetonitrile, and the reaction mixture is refluxed for 12hours after 8.3 g (0.06 mol) of potassium carbonate and 4.4 g (0.02 mol)of 4,6-dimethoxy-2-methylsulphonyl-pyrimidine have been added. Thecooled mixture is filtered, the filtrate is concentrated, the residue istaken up in 100 ml of ethanol/water (vol. 1:1) and stirred for 3 hoursat 60° C. after 2 ml of concentrated hydrochloric acid have been added.The mixture is concentrated, the residue is stirred with saturatedsodium hydrogen carbonate solution, and the crystalline product isisolated by filtering off with suction. 4.9 g (86% of theory) of4-amino-5-methylthio-2-(4,6-dimethoxy-pyrimidin-2-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one ofmelting point 198° C. are obtained.

EXAMPLE (II-4) ##STR384##

A mixture cf 3.0 g (0.03 mol) of4-amino-2,4-dihydro-3H-1,2,4-triazol-3-one, 8.7 g (0.03 mol) of2-methanesulphonyl-4,6-bis-difluoromethoxy-pyrimidine and 12.4 g (0.09mol) of potassium carbonate in 100 ml of dioxane is heated at 60° C. forapproximately 4 hours with stirring The mixture is concentrated invacuo, the residue is stirred with water, and the insoluble precipitateis filtered off with suction and washed to neutrality using highlydilute hydrochloric acid and water. After drying, 7.0 g (0.0226 mol =75%of theory) of4-amino-2-(4,6-bis-difluoromethoxy)pyrimidin-2-yl-2,4-dihydro-3H-1,2,4-triazol-3-oneof melting point 195° C. remain.

The compounds of the formula (II) which are listed in Table 3 below canbe prepared analogously to Examples (II-1) to (II-4).

                                      TABLE 3                                     __________________________________________________________________________    Preparation examples of the starting substances of the formula (II)            ##STR385##                               (II)                                Ex. No.                                                                             R.sup.3                                                                              R.sup.4                                                                             X  Y   Z        Melting point (°C.)                 __________________________________________________________________________    II-5  C(CH.sub.3).sub.3                                                                    OCH.sub.3                                                                           N  CH  COCH.sub.3                                                                             205                                        II-6  CF.sub.3                                                                             OCH.sub.3                                                                           N  CH  COCH.sub.3                                                                             213                                        II-7  C.sub.2 H.sub.5                                                                      OCH.sub.3                                                                           N  CH  COCH.sub.3                                                                             167                                        II-8  C.sub.3 H.sub.7                                                                      OCH.sub.3                                                                           N  CH  COCH.sub.3                                                                             183                                        II-9  CH(CH.sub.3).sub.2                                                                   OCH.sub.3                                                                           N  CH  COCH.sub.3                                                                             206                                        II-10 CH.sub.3                                                                             CH.sub.3                                                                            N  CH  CCH.sub.3                                                                              310                                        II-11 H      OCH.sub.3                                                                           N  CH  CNHCH.sub.3                                         II-12 H      OCH.sub.3                                                                           N  N   COCH.sub.3                                          II-13 CH.sub. 3                                                                            OCH.sub.3                                                                           N  N   CCH.sub.3                                           II-14 CH.sub.3                                                                             Cl    N  CH  COCH.sub.3                                          II-15                                                                                ##STR386##                                                                          OCH.sub.3                                                                           N  CH  COCH.sub.3                                          II-16                                                                                ##STR387##                                                                          OCH.sub.3                                                                           N  CH  COCH.sub.3                                          II-17 CH.sub.3                                                                             OCHF.sub.2                                                                          N  CH  COCHF.sub.2                                                                            255                                        __________________________________________________________________________

Starting substances of the formula (IV) EXAMPLE (IV-1) ##STR388##

10.0 g (0.088 mol) of 4-amino-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 50 ml of dry pyridine, the mixture iscooled to -10° C., and 32.7 g (0.12 mol) of2-trifluoromethoxy-benzenesulphonyl chloride are added. The reactionmixture is allowed to reach room temperature (approximately 20° C.) andstirred for approximately 12 hours. After the mixture has beenconcentrated, the residue is taken up in methylene chloride and shakenwith 1N hydrochloric acid and then with water. The organic phase isdried with sodium sulfate and filtered. The solvent is carefullydistilled off from the filtrate under a water pump vacuum. 23.1 g (80%of theory) of4-(2-trifluoromethoxy-phenylsulphonylamino)-5-methyl-2,4-dihydro-3H-1,2,4-triazol-3-oneare obtained as an oily residue.

¹ H-NMR*): (DMSO, δ, ppm): 2.10 (s, CH₃), 7.55, 7.83, 7.93 (m, 4H),approximately 11.5 (m, 2xNH).

The compounds of the formula (IV), which are listed in Table 4 below,can be prepared analogously.

                                      TABLE 4                                     __________________________________________________________________________    Preparation Examples of the starting substances of the formula (IV)            ##STR389##                            (IV)                                   Example No.                                                                          R.sup.1   R.sup.2      R.sup.3                                                                          Physical data                                __________________________________________________________________________    IV-2                                                                                  ##STR390##                                                                             H            CH.sub.3                                                                         NMR: 2.04.sup.a)                             IV-3                                                                                  ##STR391##                                                                             H            CH.sub.3                                                                         NMR: 2.04.sup.a)                             IV-4                                                                                  ##STR392##                                                                             H            CH.sub.3                                                                         NMR: 2.11.sup.a)                             IV-5                                                                                  ##STR393##                                                                              ##STR394##  CH.sub.3                                                                         M.p.: 180-190° C.                     IV-6                                                                                  ##STR395##                                                                             H            CH.sub.3                                                                         M.p.: 206-207° C.                     __________________________________________________________________________     .sup.a) 1 HNMR (DMSO, δ, ppm) for R.sup.3 = CH.sub.3               

a) ¹ H-NMR (DMSO, δ, ppm) for R³ =CH₃

Starting substances of the formula (XI) EXAMPLE (XI-1) ##STR396##

A mixture of 4.0 g (0.04 mol) of 5-methyl-1,3,4-oxadiazol-2(3H)-one, 8.8g (0.047 mol) of 4,6-dimethoxy-2-methylsulphonyl-pyrimidine, 16.9 g(0.12 mol) of potassium carbonate and 100 ml of acetonitrile is stirredfor 4 hours at 60° C. The cold mixture is concentrated under a waterpumpvacuum, the residue is stirred with water, and the crystalline productis isolated by filtering off with suction.

4.8 g (50% of theory) of3-(4,6-dimethoxypyrimidin-2-yl)-5-methyl-1,3,4-oxadiazol-2(3H)-one ofmelting point 158° C. are obtained.

USE EXAMPLES

In the following Use Examples, the compound listed below is used ascomparison substance: ##STR397##

4-(3-trifluoromethoxy-benzylideneamino)-2,4-dihydro-3H-1,2,4-triazol-3-one(disclosed in U.S. Pat. No. 3,884,910).

EXAMPLE A Post-emergence test

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Test plants which have a height of 5-15 cm are sprayed with thepreparation of the active compound in such a way as to apply theparticular amounts of active compound desired per unit area. Theconcentration of the spray liquor is chosen such that the particularamounts of active compound desired are applied in 2,000 of water/ha.After three weeks, the degree of damage to the plants is rated in %damage in comparison to the development of the untreated control. Thefigures denote

0%=no action (like untreated control)

100%=total destruction

In this test, for example, the compounds according to PreparationExamples: (1), (2), (3), (4), (92), (208) and (210) show a clearlysuperior activity compared with the prior art.

Example B Pre-emergence test

Solvent: 5 parts by weight of acetone.

Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amount of solvent, thestated amount of emulsifier is added and the concentrate is diluted withwater to the desired concentration.

Seeds of the test plants are sown in normal soil and, after 24 hours,watered with the preparation of the active compound. It is expedient tokeep constant the amount of water per unit area. The concentration ofthe active compound in the preparation is of no importance, only theamount of active compound applied per unit area being decisive. Afterthree weeks, the degree of damage to the plants is scored in % damage incomparison to the development of the untreated control. The figuresdenote:

0%=no action (like untreated control)

100%=total destruction

In this test, for example the compounds of Preparation Examples: (1),(2), (3), (4), (208) and (210) have a clearly superior activity comparedwith the prior art.

It will be appreciated that the instant specification and claims are setforth by way of illustration and not limitation, and that variousmodifications and changes may be made without departing from the spiritand scope of the present invention.

What is claimed is:
 1. A compound of the formula ##STR398## in which R¹represents the radical ##STR399## where R⁷ and R⁸ are identical ordifferent and represent hydrogen, fluorine, chlorine, bromine, iodine,cyano, nitro, C₁ -C₆ -alkyl (which is optionally substituted byfluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁-C₄ -alkylaminocarbonyl, di-(C₁ -C₄ -alkyl)aminocarbonyl, hydroxyl, C₁-C₄ -alkoxy, formyloxy, C₁ -C₄ -alkyl-carbonyloxy, C₁ -C₄-alkoxycarbonyloxy, C₁ -C₄ -alkylamino-carbonyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, di-(C₁ -C₄-alkyl)aminosulphonyl, C₃ -C₆ -cycloalkyl or phenyl), represent C₂ -C₆-alkenyl (which is optionally substituted by fluorine, chlorine,bromine, cyano, C₁ -C₄ -alkoxycarbonyl, carboxyl or phenyl), representC₂ -C₆ -alkenyl (which is optionally substituted by fluorine, chlorine,bromine, cyano, C₁ -C₄ -alkoxy-carbonyl, carboxyl or phenyl), representC₁ -C₄ -alkoxy (which is optionally substituted by fluorine, chlorine,bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl, C₁ -C₄ -alkoxy, C₁-C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl),represent C₁ -C₄ -alkylthio (which is optionally substituted byfluorine, chlorine, bromine, cyano, carboxyl, C₁ -C₄ -alkoxy-carbonyl,C₁ -C₄ -alkylthio, C₁ -C₄ -alkylsulphinyl or C₁ -C₄ -alkylsulphonyl),represent C₃ -C₆ -alkenyloxy (which is optionally substituted byfluorine, chlorine, bromine, cyano or C₁ -C₄ -cyano or C₁ -C₄-alkoxy-carbonyl), represent C₂ -C₆ -alkenylthio (which is optionallysubstituted by fluorine, chlorine, bromine, cyano, nitro, C₁ -C₃-alkylthio or C₁ -C₄ -alkoxycarbonyl), C₃ -C₆ -alkinyloxy, C₃ -C₆-alkinylthio or represent the radical --S(O)_(p) --R⁹, whereP representsthe numbers 1 or 2 and R⁹ represents fluorine, C₁ -C₄ alkyl (which isoptionally substituted by fluorine, chlorine, bromine, cyano or C₁ -C₄-alkoxy-carbonyl), C₃ -C₆ -alkenyl, C₃ -C₆ -alkinyl, C₁ -C₄ -alkoxy, C₁-C₄ -alkoxy-C₁ -C₄ -alkylamino, C₁ -C₄ -alkylamino, di-(C₁ -c₄-alkyl-amino or represents the radical --NHOR¹⁰, whereR¹⁰ represents C₁-C₆ -alkyl (which is optionally substituted by fluorine, chlorine,cyano, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄ -allylsulphinyl, C₁ -C₄-alkylsulphonyl, C₁ -C₄ -alkyl-carbonyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄-alkylaminocarbonyl or di-(C₁ -C₄ -alkyl)amino-carbonyl), represents C₃-C₆ -alkenyl (which is optionally substituted by fluorine, chlorine orbromine), C₃ -C₆ -alkinyl, C₃ -C₆ -cycloalkyl, C₃ -C₆ -cycloalkyl-C₁ -C₂-alkyl, phenyl-C₁ -C₂ -alkyl (which is optionally substituted byfluorine, chlorine, nitro, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy or C₁-C₄ -alkoxy-carbonyl), represents benzyhydryl or represents phenyl(which is optionally substituted by fluorine, chlorine, nitro, cyano, C₁-C₄ -alkyl, trifluoromethyl, C₁ -C₄ -alkoxy, C₁ -C₂ -fluoroalkoxy, C₁-C₄ -alkylthio, trifluoromethylthio or C₁ -C₄ -alkoxycarbonyl), R⁷and/or R⁸ furthermore represent phenyl or phenoxy, C₁ -C₄-alkylcarbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄-alkylaminocarbonyl-amino, di-(C₁ -C₄ -alkyl)-aminocarbonylamino, orrepresent the radical --CO--R¹¹, whereR¹¹ represents C₁ -C₆ -alkyl, C₁-C₆ -alkoxy, C₃ -C₆ -cycloalkoxy, C₃ -C₆ -alkenyloxy, C₁ -C₄ -alkylthio,C₁ -C₄ -alkylamino, C₁ -C₄ -alkoxyamino, C₁ -C₄ -alkoxy-C₁ -C₄alkyl-amino or di-(C₁ -C₄ -alkyl)-amino (which are optionallysubstituted by fluorine and/or chlorine), R⁷ and/or R⁸ furthermorerepresent C₁ -C₄ -alkylsulphonyloxy, di-(C₁ -C₄-alkyl)-aminosulphonylamino or the radical --CH═N--R¹², whereR¹²represents C₁ -C₆ -alkyl which is optionally substituted by fluorine,chlorine, cyano, carboxyl, C₁ -C₄ -alkoxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl or C₁ -C₄ -alkylsulphonyl, represents benzyl which isoptionally substituted by fluorine or chlorine, represents C₃ -C₆-alkenyl or C₃ -C₆ -alkinyl, each of which is optionally substituted byfluorine or chlorine, represents phenyl which is optionally substitutedby fluorine, chlorine, bromine, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy,trifluoromethyl, trifluoromethoxy or trifluoromethylthio, represents C₁-C₆ -alkoxy, C₃ -C₆ -alkenoxy, C₃ -C₆ -alkinoxy or benzyloxy, each ofwhich is optionally substituted by fluorine and/or chlorine, representsamino, C₁ -C₄ -alkylamino, di-(C₁ -C₄ -alkyl)-amino, phenylamino, C₁ -C₄-alkyl-carbonylamino, C₁ -C₄ -alkoxy-carbonylamino, C₁ -C₄-alkylsulphonylamino or represents phenylsulphonylamino which isoptionally substituted by fluorine, chlorine, bromine or methyl, orwherefurthermore R¹ represents the radical ##STR400## where R¹³ representshydrogen or C₁ -C₄ -alkyl,R¹⁴ and R¹⁵ are identical or different andrepresent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄-alkyl (which is optionally substituted by fluorine and/or chlorine), C₁-C₄ -alkoxy (which is optionally substituted by fluorine and/orchlorine), carboxyl, C₁ -C₄ -alkoxycarbonyl, C₁ -C₄ -alkylsulphonyl ordi-(C₁ -C₄ -alkyl)-aminosulphonyl; where furthermore R¹ represents theradical ##STR401## where R¹⁶ and R¹⁷ are identical or different andrepresent hydrogen, fluorine, chlorine, bromine, nitro, cyano, C₁ -C₄-alkyl (which is optionally substituted by fluorine and/or chlorine) orC₁ -C₄ -alkoxy (which is optionally substituted by fluorine and/orchlorine); R² represents hydrogen or the group --SO₂ --R¹, andin whichfurthermore R³ represents hydrogen, fluorine, chlorine, bromine, iodine,hydroxyl, mercapto, amino or an optionally fluorine- and/orchlorine-substituted radical selected from the group consisting of C₁-C₄ -alkyl, C₃ -C₆ -cycloalkyl, benzyl, phenyl, C₁ -C₄ -alkoxy, C₃ -C₄-alkenyloxy, C₃ -C₄ -alkinyloxy, C₁ -C₄ -alkylthio, C₁ -C₄-alkylsulphinyl, C₁ -C₄ -alkylsulphonyl, C₃ -C₄ -alkenylthio, C₃ -C₄-alkinylthio, benzyloxy, benzylthio, C₁ -C₄ -alkylamino and di-(C₁ -C₄-alkyl)-amino.
 2. A compound or salt thereof of the formula ##STR402##in which R¹ represents the radical ##STR403## where R⁷ representsfluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy,difluoromethoxy, trifluoromethoxy, C₁ -C₃ -alkylthio, C₁ -C₃-alkylsulphinyl, C₁ -C₃ -alkylsulphonyl, dimethylaminosulphonyl,N-methoxy-N-methylaminosulphonyl, phenyl, phenoxy or C₁ -C₃-alkoxycarbonyl andR⁸ represents hydrogen, fluorine or chlorine; orwhere furthermore R¹ represents the radical ##STR404## where R¹³represents hydrogen,R¹⁴ represents fluorine, chlorine, bromine, methyl,methoxy, difluoromethoxy, trifluoromethoxy, ethoxy, methoxycarbonyl,ethoxycarbonyl, methylsulphonyl or dimethylaminosulphonyl and ¹⁵represents hydrogen; where furthermore R² represents hydrogen or for thegroup --SO₂ --R¹, and R³ represents hydrogen, methyl, ethyl, propyl,isopropyl, trifluoromethyl, cyclopropyl, benzyl, phenyl, t-butyl,s-butyl, i-butyl, n-butyl, methoxy or methylthio.